Oxidation of Amines with 2-Sulfonyloxaziridines (Davis' Reagents)

Article abstract of DOI:10.1021/jo00260a012

2-(Phenylsulfonyl)-3-aryloxaziridines (Davis' Reagents) react rapidly with amines that are more basic than pyridine to give products that are dependent upon the structure of the amine.Tertiary aliphatic amines are oxidized to the corresponding N-oxides in high yields, while secondary aliphatic amines give the N,N-disubstituted hydroxylamines and corresponding nitrones in variable, stoichiometrically dependent ratios.Primary aliphatic amines give 10-35percent yields of nitroso compounds and 50-65percent yields of N-arylideneamines formed by the transimination reaction of the amine with the N-arylidenebenzenesulfonamide generated following oxygen transfer from the 2-(phenylsulfonyl)-3-aryloxaziridine.